m-Chloroperbenzoic acid → HCID 14178554, compound

HRID 477904Notes

Reaction equation

HRID 477904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[S:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:21].ClC1C=CC=C(C(OO)=[O:38])C=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[S:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:38])=[O:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14223737HCID 14223737, compound

Product 1

HCID 14178554HCID 14178554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (-)-4-(2-chlorophenyl)-3-(4-methoxyphenyl)sulfinyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine (1.4 g), prepared as in Preparation II above, in dichloromethane (300 ml), cooled to 0° C., was added m-chloroperbenzoic acid (660 mg). After stirring for 24 hours, the reaction mixture was washed with aqueous NaHCO3, dried over MgSO4, and evaporated to dryness. The residue was chromatographed on silica gel (1:1 dichloromethane/ethyl acetate) and recrystallized from dichloromethane/hexane to give (-)-4-(2-chlorophenyl)-3-(4-methoxyphenyl)sulfonyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine, m.p. 200°-202° C., [α]D =-126° (C=0.031, methanol) [93% enantiomeric excess (ee)].

Workup

  1. washthe reaction mixture was washed with aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was chromatographed on silica gel (1:1 dichloromethane/ethyl acetate)
  5. customrecrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-c1702d0df63e4f3da998f73b444d9ed1
Source dataset
uspto-grants-1989_12
Patent number
US04889866

Reaction notes

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